Dimethylformamide → 5-{4-[2-(5-Benzyl-2-oxooxazolidin-3-yl)propoxy]benzyl}thiazolidine-2,4-dione

HRID 1901662Notes

Reaction equation

HRID 1901662 reaction equation
[C:1]1([CH2:7][CH:8]([OH:29])[CH2:9][NH:10][CH:11]([CH3:28])[CH2:12][O:13][C:14]2[CH:27]=[CH:26][C:17]([CH2:18][CH:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)[CH:32]=[O:33]>>[CH2:7]([CH:8]1[O:29][C:32](=[O:33])[N:10]([CH:11]([CH3:28])[CH2:12][O:13][C:14]2[CH:27]=[CH:26][C:17]([CH2:18][CH:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[CH:16][CH:15]=2)[CH2:9]1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 98019075-{4-[2-(3-Phenyl-2-hydroxypropylamino)propoxy]benzyl}thiazolidine-2,4-dione

Product 1

HCID 214748085-{4-[2-(5-Benzyl-2-oxooxazolidin-3-yl)propoxy]benzyl}thiazolidine-2,4-dione

Procedure

Following a procedure similar to that described in Example 4, 300 mg of 5-{4-[2-(3-phenyl-2-hydroxypropylamino)propoxy]benzyl}thiazolidine-2,4-dione (prepared as described in Example 7), 120 mg of N,N'-carbonyldiimidazole and 10 ml of anhydrous dimethylformamide were used. The resulting crude product was applied to a silica gel chromatography column, which was then eluted with a 3:2 by volume mixture of ethyl acetate and hexane, to give 200 mg of the title compound, melting at 60° C. to 70° C.

Workup

  1. washwas then eluted with a 3:2 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-5bd9f587d4164b2191919785fa213871
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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